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ES479576A1 - Un procedimiento para la preparacion de 4-aza-5-andostran-3 ona 17 sustituida. - Google Patents

Un procedimiento para la preparacion de 4-aza-5-andostran-3 ona 17 sustituida.

Info

Publication number
ES479576A1
ES479576A1 ES479576A ES479576A ES479576A1 ES 479576 A1 ES479576 A1 ES 479576A1 ES 479576 A ES479576 A ES 479576A ES 479576 A ES479576 A ES 479576A ES 479576 A1 ES479576 A1 ES 479576A1
Authority
ES
Spain
Prior art keywords
product
androstan
treating
methyl
17beta
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES479576A
Other languages
English (en)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of ES479576A1 publication Critical patent/ES479576A1/es
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0016—Oximes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J33/005—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
    • C07J33/007—Cyclic thioketals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0066—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by a carbon atom forming part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
    • C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
    • C07J73/005—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Un procedimiento para la preparación de 4-aza- 5alfa-androstan-3-ona 17 sustituida, de fórmula: **(Fórmula)** cuyo procedimiento comprende las siguientes etapas: 1) hacer reaccionar la pregnenolona con yodo y piridina para formar el correspondiente derivado yoduro de 20-piridinio de la pregnenolona; 2) hacer reaccionar el producto de la etapa (1) con metanol para formar el éster metílico del 17- carboxiandrostenol; 3) tratar el producto de la etapa (2) con isopropóxido de aluminio y ciclohexanona para formar 4-androstan-3-ona-17-carboxilato de metlio; 4) hidrolizar el producto de la etapa (3) para formar el correspondiente compuesto 17-ácido; 5) tratar el producto de la etapa (4) con el complejo de cloruro de oxalilo; piridina para formar el correspondiente compuesto 17-cloruro de ácido; 6) tratar in situ el producto de la etapa (5) con dietilamina para formar 17beta-N,N- dietilcarbamoil-4-androstan-3-ona; 7) oxidar el producto de la etapa (6) con peryodato sódico y permanganato potásico en un sistema disolvente de terbutanol: agua para formar el correspondiente compuesto ácido 5-oco-3, 5- seco-androstan-3-oico; 8) tratar el producto de la etapa (7) con metilamina en etilenglicol para formar 17beta-N, N-dietilcarbamoil-4-metil-4-aza-5-androsten-3-ona; 9) hidrogenar el producto de la etapa (8) tratándolo con hidrógeno en condiciones catalíticas para formar el producto final, 17beta- N,N-dietilcarbamoil-4-metil-4-aza-5alfa-androstan- 3-ona.
ES479576A 1978-04-13 1979-04-11 Un procedimiento para la preparacion de 4-aza-5-andostran-3 ona 17 sustituida. Expired ES479576A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/896,120 US4179453A (en) 1978-04-13 1978-04-13 Process for preparing 17β-carboxy-5-androsten-3-ones

Publications (1)

Publication Number Publication Date
ES479576A1 true ES479576A1 (es) 1979-12-01

Family

ID=25405660

Family Applications (1)

Application Number Title Priority Date Filing Date
ES479576A Expired ES479576A1 (es) 1978-04-13 1979-04-11 Un procedimiento para la preparacion de 4-aza-5-andostran-3 ona 17 sustituida.

Country Status (11)

Country Link
US (1) US4179453A (es)
AR (7) AR231991A1 (es)
AT (1) AT377767B (es)
DK (2) DK165325C (es)
ES (1) ES479576A1 (es)
FI (1) FI67389C (es)
GR (1) GR68531B (es)
NO (1) NO153141C (es)
PL (2) PL126826B1 (es)
PT (1) PT69451A (es)
YU (1) YU86879A (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5237061A (en) * 1988-10-31 1993-08-17 Merck & Co., Inc. Methods of synthesizing benign prostatic hypertropic agents and their intermediates
US4937237A (en) * 1988-12-23 1990-06-26 Smithkline Beckman Corporation Phosphinic acid substituted aromatic steroids as inhibitors of steroid 5-60 -reductase
US4970205A (en) * 1988-12-23 1990-11-13 Smithkline Beecham Corporation Sulfonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase
US5360881A (en) * 1989-06-14 1994-11-01 Societe Francaise Hoechst Method of cross-linking ethylene monomers using diallyloxyacetic acid and its basic addition salts as cross-linking agents
IE76452B1 (en) * 1990-10-29 1997-10-22 Sankyo Co Azasteroid compounds for the treatment of prostatic hypertrophy their preparation and use
FR2724174B1 (fr) * 1994-09-06 1997-01-17 Roussel Uclaf Procede de preparation d'un derive steroide 17beta-carboxy et nouveaux intermediaires

Also Published As

Publication number Publication date
PL223577A1 (es) 1981-11-27
ATA275079A (de) 1984-09-15
AR222390A1 (es) 1981-05-15
FI67389C (fi) 1985-03-11
PT69451A (en) 1979-05-01
NO791220L (no) 1979-10-16
AR231991A1 (es) 1985-04-30
AR228037A1 (es) 1983-01-14
US4179453A (en) 1979-12-18
AR225045A1 (es) 1982-02-15
AR241488A1 (es) 1992-07-31
PL126826B1 (en) 1983-09-30
NO153141C (no) 1986-01-22
NO153141B (no) 1985-10-14
FI791193A7 (fi) 1979-10-14
GR68531B (es) 1982-01-14
AT377767B (de) 1985-04-25
AR224011A1 (es) 1981-10-15
AR222391A1 (es) 1981-05-15
DK92192A (da) 1992-07-15
DK165325B (da) 1992-11-09
YU86879A (en) 1983-10-31
DK165325C (da) 1993-03-29
PL214881A1 (es) 1981-12-11
FI67389B (fi) 1984-11-30
DK92192D0 (da) 1992-07-15
DK152579A (da) 1979-10-14

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19970303